Shrinkage control of cellulosic and wool textiles with diglycidyl ether compounds



SAGE CONTROL OF CELLULOSIC AND WQOL TEXTILES WITH DIGLYCIDYL ETHER COOUNDS Tzeng .iiueq Suen, Stamford, Conn., assignor to American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing. Application August 13, 1952, Serial No. 304,229

7 Claims. (Cl. 8-116) This invention relates to a process of rendering textile materials substantially resistant to shrinkage and creasing. It is an object of the invention to provide a process for rendering cotton, wool, rayon and other fibrous textile materialscontaining functional groups substantially rewherein R is an alkylene group of from 2 to 6 carbon atoms, inclusive, drying the impregnated textile material and curing the compound in situ. Preferably one should use about -15% by weight based on the dry weight of the textile material.

The impregnation step may be conveniently accomplished by means well-known in the art, for example, the textile material may be passed through or dipped in a solution of the compound in water or any other solvent in which the compound is soluble.

The step of drying the material can be performed by any conventional means, such as by heating in a forced air dryer. However, heating is not essential for the purpose of drying and the drying may be readily accomplished by merely allowing the material to remain in contact with the atmospheric air for a short period of time.

The curing step is preferably accomplished by heating, and if desired, the drying and curing steps may be consolidated. The curing step, in theory, effects the opening of the epoxy ring in the compound thereby causing the compound to react with the functional groups of the fibrous material being treated. In this matter the compound is firmly united with the fabric and becomes insolubilized. There are no particularly critical conditions required for the curing step. The preferred temperature is from 50 C. to 200 C. The rapidity of curing can be accelerated, if desired, by incorporating a substance having a catalytic effect in the impregnating solution, a1- though this is not at all necessary. However, if it is desired to employ a catalyst, an acid or an alkali, or any substance having a latent acid or alkaline effect, will accelerate 'the cure. Thus, there may be used as catalysts compounds such as oxalic acid, sodium carbonate, aluminum chloride, ammonium chloride, diammonium phosphate or hexamethylenetetramine and the like.

In order to more fully illustrate this invention the following examples are given. Parts are by weight unless otherwise specified.

Example 1 A piece of 80 x 80 cotton percale is dipped in a 10% solution of ethylene glycol bis-glycidyl ether in water. The solution also contains 1% of a mixture containing 30 parts of diammonium phosphate and 4 parts of hexamethylenetetramine. The wet cloth is then dried by hanging it in contact with atmospheric air. By weighing the dried cloth, it is determined that 6.2% of bis-glycidyl ether based on the weight of the cloth has been picked up. Curing is efiected by heating the cloth at 350 F. for 10 minutes. The warp shrinkage of this treated cloth after washing for one hour is 3.1%. The corresponding Warp shrinkage figures for a piece of untreated cloth from the same roll after 1 hour and 3 hour washes are 6.7% and 7.9%, respectively. The crease resistance of the treated cloth is also improved.

Example 2 A piece of wool serge cloth is treated with a 10% solution of hexamethyleneglycol bis-glycidyl ether in water. The wet cloth is dried in a forced air current at 40 C. for 20 minutes. The dried cloth shows a dry pick-up of 7.5% of the hexamethyleneglycol bis-glycidyl ether. The dried cloth is heated at 300 F. for 30 minutes to effect the curing of the compound. Shrinkage tests show that the treated cloth as approximately 6 the shrinkage value of a piece of untreated cloth from the same roll.

Example 3 A piece of x 80 cotton percale is treated with a 10% solution of ethylene glycol bis-glycidyl ether in water. The solution also contains 0.5% of oxalic acid. The treated cloth, with about Wet pick-up, is dried and cured at 290 F. for 6 minutes. The warp shrinkage of this treated cloth after Washing for 1 hour is 2.5% and that after 3 hour washing is 2.8%. The correspond ing figures for the untreated cloth are 5.3% and 5.6%, respectively.

The bis-glycidyl ethers employed in this invention may be conveniently prepared by the reaction of the corresponding glycol and epichlorohydrin. For example, in the preparation of ethylene glycol bis-glycidyl ether, ethylene glycol may be condensed with an excess of epichlorohydrin in the presence of concentrated sulfuric acid as a catalyst to form the addition compound having the formula The acid catalyst may be neutralized with barium carbonate or other alkali and removed by filtration. The excess of epichlorohydrin may be removed by distillation. The addition compound can then be treated with caustic solution in Water at room temperature, whereby it is converted into the epoxy compound.

Many modifications may be made in the process without departing from the spirit and scope of the invention. For instance, other substances may be incorporated in the impregnating bath for the purpose of modifying the hand of the textile material or far the purpose of ren dering the material water-repellent. Other modifications will be apparent to those skilled in the art.

Amongst the compounds which can be used to treat the textile materials in accordance with the present invention are ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, trimethylene glycol diglycidyl ether, 1,4- butanediol diglycidyl ether, 1,3-butanediol diglycidyl ether, 2,3-butanediol diglycidyl ether, 1,5-pentanediol diglycidyl ether, 2,4-pentanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 2,5-hexanediol diglycidyl ether, 2-methyl-2,4-pentanediol diglycidyl ether and the like.

I claim:

1. A process of impregnating a textile material selected from the group consisting of cellulosic and wool materials, said process comprising impregnating said textile material with an aqueous solution of a compound having the formula where R is. an alkylene radical of from 2 to 6 carbon atoms in sufficient amount to deposit on said textile material between about 2 and about 30 per cent of said compound based on the dry weight of said textile material, drying said impregnated material and curing said compound to a Water-insoluble state by heating at a temperature between about 50 and about 200 degrees centigrade to produce a flexible shrink-resistant textile material.

2. The process of claim 1 in which said compound is ethylene glycol bis-glycidyl ether.

3. The process of claim 1 in which said textile material comprises cotton.

4. The process of claim 1 in which said deposit amounts to between about and about per cent of the dry weight of said textile material.

5. The process of claim 1 in which said aqueous solution contains a curing catalyst for said ether compound.

6. A process which comprises impregnating a cotton fabric with an aqueous solution of ethylene glycol bisglycidyl ether in sufiicient amount to deposit between about 5 and about 15 per cent of said ether based on the dry weight of said cotton fabric, drying said impregnated cotton fabric and curing said ether to a Water-insoluble state by heating at a temperature between about and about 200 degrees Centigrade to produce a flexible shrinkresistant cotton fabric.

7. A process which comprises impregnating a wool fabric with an aqueous solution of ethylene glycol bisglycidyl ether in sufiicient amount to deposit between about 5 and about 15 per cent of said ether based on the dry weight of said woolen fabric, drying said impregnated wool fabric and curing said ether to a water-insoluble state by heating at a temperature between about 50 and about 200 degrees centigrade to produce a flexible shrinkresistant wool fabric.

References Cited in the file of this patent UNITED STATES PATENTS 2,131,120 Schlack Sept. 27, 1938 2,252,039 Schirm Aug. 12, 1941 2,500,449 Bradley Mar. 14, 1950 2,500,600 Bradley Mar. 14, 1950 2,606,810 Erickson et al. Aug. 12, 1952 

1. A PROCESS OF IMPREGNATING A TEXTILE MATERIAL SELECTED FROM THE GROUP CONSISTING OF CELLULOSIC AND WOOL MATERIALS, SAID PROCESS COMPRISING IMPREGNATING SAID TEXTILE MATERIAL WITH AN AQUEOUS SOLUTION OF A COMPOUND HAVING THE FORMULA 